Knowing what we know now about Giuliani and '08 itself, he really underperforms expectations. He would struggle with the shifting of the focus of the race from national security to the economy, personal scandals, charges of inexperience made worse by a VP pick attempting to sate grassroots conservatives, and overall just fumbling the campaign. Giuliani takes the problems of the McCain campaign and piles more on, and against a candidate who, while not as "country" as some users like to pretend, would have a stronger appeal in rural areas than Obama. No, not West Virginia, that ship sailed around 2000 with the Democrats' embrace of environmentalists. But definitely Missouri.
Fmr. Mayor Rudy Giuliani (R-NY) / Governor Sarah Palin (R-AK)
Senator Hillary Clinton (D-NY) / Senator Evan Bayh (D-IN) ✓